I have been in the bowl for a month or so now and after a few bad experiences (typical ghosting, but also got stood up completely on one date!) I now after being persistent I have two very lovely POTs and I am about to have second dates with both of them (two nights in a row!). I have not talked about specifics of an arrangement with either of them. Ultimately I am looking for an allowance and not tonnes of shopping and gifts. I have a good sense of what I am looking for in terms of amount. Although I am open to the possibility of seeing them both, I would prefer to be exclusive with one person, as realistically two guys will be hard to juggle – I am terrible at it in the vanilla world already lol! Is it right to think that if the POT also wants exclusivity, that is worth more in terms of allowance especially if he asks for it? What are your thoughts on bringing up allowance on the second date? (If it matters, first date with POT #1 was more of a true M&G as we just had cocktails, POT #2 was drinks that turned into dinner). Both have subtly expressed their dislike for the ‘transactional’ nature of SR’s so I am hesitant to push too much. Truthfully, if I can come to agreement with either of them (although I do have a slight preference for one of them) I would stop seeing the other. I do not want to mislead either of them or put them against each other. If nothing comes up naturally on the second date should I go on a third date and hope the conversation happens given third date is where they will likely expect intimacy? Or should I be bold and bring it up myself since I do have ‘options’ and surely one of the two of them will be ready and willing to come to an agreement on the second date?

Most SDs already have a good idea of how much allowance they’re prepared to offer and how much time they’d like to spend together. Personally, I wouldn’t offer a higher allowance for exclusivity, but if I thought you were planning on seeing multiple SDs I may not go forward with an arrangement as I’d be more concerned over your time management. Are you going to cancel on our date for another offer? I can’t guarantee ( or expect ) that you’ll be exclusive to me anyway, so it would be foolish to offer a higher allowance on that basis. But if you tell me (convincingly) that you’re only looking for one SD, I may be more likely to choose you.

You definitely have to have had the allowance conversation and agreement before a date when intimacy may occur. If he doesn’t bring it up on the second date, you have to. Sure, it can feel awkward the first time, but you have to directly state – “I’m looking for an allowance” ( of course, this should be surrounded by flirting and flattery about how excited you are get to know him better etc. ). If he’s a gentleman, he’ll come back with an offer, but you should already have some numbers in mind yourself. Don’t be afraid to tell him what you’re looking for. If he’s genuine about this, he’s not going to be offended. If he acts offended, he was never genuine anyway.

My advice – don’t try and play the two POTs against each other. Go all out for POT1 on the first night. If he makes you an offer, you can accept it and still go on a date with POT2 the following night. If POT2s offer is better, and particularly if he was the one you had a preference for anyway, you can make your apologies to #1 and tell him that you’ve decided not to progress the SR. You don’t need to tell him that you’ve received a better offer. An arrangement only really starts when an allowance changes hands.

Be wary about guys saying they don’t like the transactional nature of SRs. A transaction comes with the territory. And lets face it, all relationships are ‘transactional’. We date people because of what we get out of it – great sex, interesting conversations, emotional support, parent for our future children etc. If our vanilla partners didn’t provide those things, we wouldn’t stay with them. In a successful relationship, you (try to) provide what the other party needs. SRs just require that transaction to be clearly stated upfront.

You got great advice from @inamorato. I want to reinforce the point about bringing up allowance. Any SD worth s date will expect and deal with the topic gracefully.

Now, I want to address the transactional comment. First, @inamorato is right, it can be a warning sign. However, I dislike arrangements appearing transactional …. which means explicitly or purely transactional. So I make sure it is not. I provide an allowance. Second, I give her a card with her allowance early in the date, so she has time to take it, check it, and that after dinner, etc., she has an ability to end the evening. It means I risk being out the allowance. It has happened to me once. Yes, it pisses me off, but it’s worth it since I am looking for an ongoing long term sugar relationship.

That’s a long answer to say, great, they don’t want it to be transactional. He bloody well can structure things do it does not feel that way for him and still be gracious for the SB.

Thank you so much for the very thoughtful and helpful responses @inamorato and @sfwinefan. As an update, POT #1 had to cancel due to travel but we are rescheduled this week. I am looking forward to seeing him as we had a great connection at our first meeting.

POT #2 and I met for drinks and to watch basketball playoffs (his suggestion which I loved!). Conversation flowed freely but I from his body language I felt that he was feeling either a bit shy or nervous, or maybe potentially unsure about attraction. I was trying to flirt (touching his arm, complimenting him very sincerely) and he wasn’t really flirting back. It didn’t feel right to bring up an arrangement. I’ve seen a few others post that some SD’s take 3 to 5 dates to decide if they want to move into an SR and I think he may be one of them. He is also newish (one very short Arrangement previously – I don’t know the details)
We had a quick kiss at the end of the date before he put me in a cab. We haven’t chatted since but I plan to message him to see if he wants to meet again. I enjoy his company so I don’t mind having a couple more dates to see where it goes.

Have I totally lost my window of opportunity? I don’t want to make the same mistake with POT #2!

Generally, the sugarbowl is accelerated dating. Some SDs might be happy with 3-5 platonic dates, but for the vast majority it’s much faster. The chances are, he has other POTs lined up and is seeing who is the best fit before making a move. There’s definitely no harm in sending him a message after the date to say how much you enjoyed his company, and a ‘reminder’ in a few days time. There’s some role reversal here, so you need to be doing the chasing whilst still trying to make him feel in control.

As a counter to @ciaobella, I never have this resolved before the first meeting ;-). Sometimes, POTs have told me what kind of allowance they expect, and if it wasn’t outlandish I’ve told them that wouldn’t be a problem. But, I’ve never made an offer of allowance before meeting someone. Generally over text after the M&G. Sometimes during a first date. Always before a date where intimacy was a possibility. If she genuinely enjoyed my company ( and if she doesn’t, I don’t want to be with her ), she should be able to cope with a couple of dates where I cover all the expenses but she doesn’t receive an allowance.

@waterbaby82, a couple of things. First, if you’re not getting the attraction vibe, I might look at that as a warning sign. He may be interested in the hot date more than an arrangement. Second, ask him the details on why the last arrangement was short. If he is unsure, smile, do a flirting move that works for you, and tell him you don’t want to make the same mistakes she did. 😋

It sounds like you did everything right. However in my mind waiting 3 to 5 dates to mail things down is just wasting both our time.